Hopefully it is clear that you should ask and communicate. 😀
With a little lubricant it is definitely easier and more fun. If I do it myself while jerking off, then the finger goes in quite well without lubricant, but if the woman does it, please do so with a little moisture.
Playing at the hole is also very exciting and you don't always have to push something in.
No. I've tried prostate massage, and it does absolutely nothing for me. It's not painful, but it's also not enjoyable; it mostly just feels mildly awkward. I genuinely do not see what gay men get out of it on the receiving end.
The idea that all men likes it, and men that don't like it just haven't tried it correctly yet is just... Dumb. Like, it's a level of stupid that's on the order of insisting that lesbians just haven't had the right dick yet.
I certainly find it tricky. I don't think I've achieved it yet. All I've managed so far is make it feel more intense. I haven't figured out what I'm doing wrong.
I haven't tried a plug too much but my wife has done a finger during a blowjob which I enjoyed. It amplifies the pleasure of the blowjob. I don't really enjoy it on its own. I find stimulation of the perineum and base of the cock is similarly enjoyable.
Also I don't enjoy in and out sensation too much. It feels like I'm pooping. Just the pressure of it being in.
Yes with proper lubrication. Just playing around with the finger tip is amazing! A plug can also be great. Past a few inches you're nearing "train for it" territory and it may start to be uncomfortable or painful. Everyone needs to learn their body and its limits ofc.
I like it. I finger myself sometimes. The last time I tried it with my previous partner, I gave her a pair of thick rubber kitchen gloves so her manicured nails wouldn't be a hygiene issue. She used oil-based lube and stuck a couple fingers in. It didn't feel great, but I would have preferred she continue rather than stopping at the slightest sign of discomfort. Pain and nonconsent are my kinks, but I've accepted that few people are true sadists.
I haven't had as many male partners, nor have my male relationships lasted as long. It's not that I don't like guys, but my type is more effeminate and cute while still dominant. Very, very few people like that in the world.